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WO1986004057A1 - Production de composes de carbonyle superieur a partir d'alcools inferieurs - Google Patents

Production de composes de carbonyle superieur a partir d'alcools inferieurs Download PDF

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Publication number
WO1986004057A1
WO1986004057A1 PCT/GB1985/000593 GB8500593W WO8604057A1 WO 1986004057 A1 WO1986004057 A1 WO 1986004057A1 GB 8500593 W GB8500593 W GB 8500593W WO 8604057 A1 WO8604057 A1 WO 8604057A1
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Prior art keywords
process according
catalyst
alcohol
hydrogen
carbonyl compounds
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Ceased
Application number
PCT/GB1985/000593
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English (en)
Inventor
Derek Kenneth Macalpine
Bruce Leo Williams
Peter Sefton Williams
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BP Chemicals Ltd
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BP Chemicals Ltd
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Publication of WO1986004057A1 publication Critical patent/WO1986004057A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/002—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/73—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with hydrogenation

Definitions

  • This invention relates in general to the upgrading of oxygenated compounds.
  • the invention relates to the preparation of higher carbonyl compounds from lower alcohols, and optionally lower carbonyl compounds, in the presence of a ruthenium supported catalyst.
  • the invention relates to the upgrading of lower alcohols to higher alcohols in the presence of the same ruthenium supported catalyst.
  • carbonyl compounds can be prepared by reacting lower alcohols, optionally with lower carbonyl compounds, in the presence of a ruthenium metal or metal oxide supported catalyst.
  • a process for the preparation of higher carbonyl compounds from C ⁇ to Cs cyclic or acyclic alcohols containing at least one active hydrogen atom bonded to the beta carbon atom or readily convertible thereto under the reaction conditions, the process comprising reacting the alcohol in the presence of a catalyst at elevated temperatures characterised in that the catalyst is ruthenium metal or an oxide thereof supported on a solid support.
  • the alcohols of this invention are saturated cyclic or acyclic alcohols containing at least one active hydrogen atom bonded to the beta carbon atom or readily convertible thereto under the reaction conditions employed.
  • examples of alcohols include but are not limited to methanol, ethanol, propanol, butanol pentanol, hexanol or combinations thereof.
  • the alcohols may also be reacted with lower carbonyl compounds to produce the higher carbonyl compounds.
  • Useful lower carbonyl compounds are ketones or aldehydes having from 1 to 4 carbon atoms such as dimethyl ketone (acetone), ethyl methyl ketone, formamide, and the like.
  • the alcohol used in the above reaction to produce higher carbonyl compounds can be replaced by a lower carbonyl compound and a suitable amount of hydrogen.
  • a lower carbonyl compound and a suitable amount of hydrogen for example, in the preparation of methyl isobutyl ketone, isopropanol can be replaced with a suitable mixture of acetone and hydrogen.
  • the ratio of lower carbonyl compound to hydrogen can vary from 3:1 to 1:1.
  • the higher carbonyl compounds prepared in accordance with this invention are aldehydes or ketones having at least one more carbon atom than the longest carbon chain alcohol or lower carbonyl compound reactant employed. These aldehydes and ketones may be saturated or unsaturated compounds and may be mono- or poly-aldehydes or ketones.
  • the preferred higher carbonyl compounds produced herein are C to saturated monoketones. Most preferred are methyl isobutyl ketone and diisobutyl ketone.
  • Higher alcohols that is alcohols having at least one additional carbon atom than the reactant alcohol, may also be formed to a greater or lesser extent, depending on the nature of the alcohol reactant, the nature of the catalyst support and the reaction conditions employed.
  • the higher alcohols can be any alcohols having at least one additional carbon than the lower alcohol reactant.
  • ethanol can be converted into a higher alcohol such as propanol or butanol. While the higher alcohols will contain at least one additional carbon atom than the lower alcohol reactant, preferably the higher alcohol will contain 2 or more additional carbons. Butanol is the most preferred higher alcohol.
  • the catalysts useful in the reactions of the present invention are ruthenium metal and metal oxide supported catalysts. Suitable supports are any solid support matrix which is either acidic or basic and having the ability to catalyse condensation reactions.
  • the preferred condensation supports used herein are the conventional aluminas, silicas, alumina-silicas or zeolites known to those skilled in the art.
  • the zeolite supports can range from the naturally occurring zeolites such as onalcite, chabazite, heulandite, natrolite, stilbite, or thomsonite or the artificially prepared zeolites such as X, Y or Linde type L.
  • the preferred zeolites are the highly acidic zeolites such as alkali metal ion-exchanged X and Y zeolites.
  • the zeolite supports can be selected to provide some shape selectivity towards certain products. For example, NaY was found to give low amounts of isopropanol from the reaction of acetone and hydrogen. However, 13 X zeolite was found to give large amounts of isopropanol in the same reaction.
  • the catalysts of this invention can be prepared by any conventional technique for incorporating metals into an inorganic support such as by impregnation or coprecipitation or by ion exchange techniques.
  • the loadings can vary from about 0.1% to about 20% by weight, preferably from 3% to 10% by weight metal, based on the weight of the support.
  • the supported ruthenium catalysts of this invention can be promoted with alkali or alkaline earth metals. These promoter metals can be present in amounts from 0.01% to 10% by weight.
  • the temperatures and pressures used in these reactions can vary widely depending on the products desired. Generally, temperatures of greater than 100°C and preferably from 150°C to 300°C are suitably employed. The pressures employed are typically ambient although pressures ranging from 0.1 bar to about 50 bar can be employed.
  • the space velocity defined as volume of liquid phase reactants per volume catalysts per hour, can also range widely. Typically, space velocities from about 0.1 to 5 are suitable with space velocities from 0.5 to 1.0 being preferred.
  • the ratio of the respective reactants can vary widely.
  • the ratio of alcohol to lower carbonyl compound can range from 10 : 1 to 1 : 10 with a ratio of 3 : 1 to 1 :3 being preferred.
  • the inventive process can be conducted in any suitable reactor in either the fluid-b&d or fixed-bed mode . "Moreover, the reaction cfen be either 'a continuous or batch-type operation.
  • One particular advantage of using the ruthenium supported catalyst is their ability to be reactivated by contacting the catalyst with water, preferably in the gaseous phase , air or hydrogen.
  • the catalyst When the catalyst begins losing activity (becomes spent) , its activity can be reinstated by contacting it with water, air or hydrogen at temperatures from between 100°C and 400°C for a period of between 1 and 300 minutes. In this manner, the catalyst used in the var_ous embodiments of this Invention can maintain high levels of activity over prolonged periods.
  • steam may be co-fed to the process on a continuous or intermittent basis for the purpose of Improving the catalyst lifetime .
  • Example 1 A commercially obtained ruthenium on an alumina support containing 5% by weight ruthenium (12.6 gms) catalyst was placed in a glass tube in an oven equipped with temperature controller and the oven temperature was maintained at 180°C. Isopropanol was pumped to a preheater at a rate of 2.6 ml/h where it was volatilised and mixed with nitrogen supplied at a rate of 30 ml/minute . Condensible products leaving the reactor were trapped in an ice/water condenser.
  • the isopropanol feed was stopped and the liquid product was recovered. It was found to comprise two layers of approximately equal weight and each was analysed using standard gas chromatography techniques and a Karl-Fische r water titration apparatus. All percentages are calculated by weight. The lowe r layer was found to contain approximately 45% water, 30% acetone , 15% isopropanol, 7% methyl isobutyl ketone (MiBK) , 2% diisobutyl ketone (DiBK) and 1% 4-methylpentan-2-ol.
  • MiBK methyl isobutyl ketone
  • DIBK diisobutyl ketone
  • the upper layer was found to contain approximately 34% acetone , 13% i sopropanol, 30% methyl isobutyl ketone , 3% 4-methylpentan-2-ol and 17% diisobutylketone .
  • Example 2
  • Example 2 The experimental procedure of Example 1 was followed except that isopropanol was replaced by a 1 .97 : 1 molar mixture of methanol and acetone .
  • the liquid feed rate was 2.56 ml/hr and the nitrogen gas flow rate was 31.2 ml/minute .
  • the liquid feed was stopped afte r 3.28 hrs .
  • Analysis of the condensate showed it to contain approximately 2.5% isopropanol, 2.5% methyl ethyl ketone and 1 .4% mesityl oxide .
  • Example 2 The experimental procedure of Example 1 was followed, except that only 8.0 g of catalyst were used and the isopropanol was replaced by ethanol.
  • the liquid feed rate was 2.5 ml/h, and the nitrogen gas feed rate was 30 ml/minute .
  • the liquid feed was stopped after 2.3 hours.
  • Analysis of the condensate showed it to contain approximately 7.0% n-butanol, 0.3% n-butanal, and small amounts of acetaldehyde , diethyl ether and ethyl acetate .
  • Example 1 The experimental procedure of Example 1 was followed except that only 2.5 g of catalyst were used. The liquid feed rate was 1.7 ml/hr and the nitrogen gas flow rate was 35.3 ml/minute. The condensed products were analysed at hourly intervals. After 12 hours, the level of MiBK had dropped from 4.8% to 1.1%. The catalyst was regenerated in situ at 330°C by feeding water into the reaction apparatus at 1.8 ml/hr and nitrogen gas at 10 ml/minute for 2 hours. After cooling under nitrogen the same reaction conditions as above were employed. The yield of MiBK increased to 16.8%. Catalyst Regenerated with Hydrogen
  • Example 4 The experimental procedure of Example 4 was followed. After 12 hours the level of MiBK had dropped from 4.4% to 1.2%. The catalyst was regenerated in situ at 230°C by feeding hydrogen gas into the reaction apparatus at 35.3 ml/minutes for 2 hours. After cooling under hydrogen the same reaction conditions as Example 4 were employed. The yield of MiBK increased to 18.9%.
  • Example 1 The experimental procedure of Example 1 was followed except that only 2.5 g of catalyst were used. The catalyst was treated in situ at 230 ⁇ C with hydrogen gas at 35.3 ml/minute for 2 hours prior to use . The ispropanol was replaced by acetone and the nitrogen by hydrogen. The liquid feed rate was 1 .8 ml/hr and the hydrogen gas flow rate was 3.33 ml/minute. Analysis of the condensed products after 2.25 hours showed it to contain 52.6% acetone , 2.0% isopropanol, 28.6% MiBK, 0.7% mesityl oxide , 0.57% 4-methylpenta ⁇ _-2-ol and 8.2% diisobutyl ketone with the balance consisting of water and minor components.
  • the zeolite was filtered, washed with distilled water until washings were free of chloride ions and dried at 80°C for 18 hours to give the product as a black powder.
  • the above catalysts were activated in situ at 400°C by treating with nitrogen, air and hydrogen. Nitrogen was passed over the catalyst at 10 1/hr for 4 hours, followed by air at 10 1/hr for 1 hour, followed by nitrogen at 10 1/hr for 1 hr, followed by hydrogen at 7 1/hr for 4 hrs. The catalysts were cooled to 180°C under hydrogen.
  • Example 1 The experimental procedure of Example 1 was followed except that the ruthenium NaY catalyst prepared and ac-ivated above (3.62g) was used. Isopropanol was replaced by acetone and nitrogen by hydrogen. The liquid feed rate was 10 ml/hr and the hydrogen gas flow rate 20 ml/minute. The condensed products were analysed at intervals. After 2.45 hours the amount of MiBK was 3.0%, DiBK 1.7% and isopropanol (IPA) 0.0%. After 14.75 hours the acetone feed rate was reduced to 3 ml/hour. For the period 16.75 hours to 18.75 hours the amount of MiBK was 10.7%, DiBK 2.1% and isopropanol 0.3%.
  • IPA isopropanol
  • Example 8 The experimental procedure of Example 7 was followed except that the ruthenium 13X catalyst prepared and activated above (3.83g) was used. The liquid feed rate was 10 ml/hour and the hydrogen gas flow 16.3 ml/minute. After 2 hours, the amount of MiBK was 4.6% , DiBK 1.4% and IPA 1.0%. After 5 hours the acetone feed rate was reduced to 2.5 ml/hr. For the period 8 to 10 hours the amount of MiBK was 11.1%, DiBK 1.7% and IPA 30.2%.
  • Example 5 Use of Steam Co-feed to Improve Catalyst Lifetime
  • the catalyst of Example 5 was used. After treating with steam for 2 hours at 330°C, the level of MiBK was 17.4%.
  • Example 1 The experimental procedure of Example 1 was followed except that isopropanol was replaced by a mixture of isopropanol and water (9: 1 vol/vol) and nitrogen fed at 35.3 ml/minute. Analysis of the condensed products at intervals showed that after 17 hours the level of MiBK had dropped from 11.9% wt to 5.8% wt.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

Des composés de carbonyle supérieur sont préparés à partir d'alcools cycliques ou acycliques C1 à C8 contenant au moins un atome d'hydrogène actif lié à l'atome bêta de carbone ou aisément transformable en celui-ci dans des conditions de réaction, en faisant réagir l'alcool en présence d'un catalyseur tel que le ruthénium ou un oxyde de celui-ci fixé sur un support solide.
PCT/GB1985/000593 1985-01-03 1985-12-19 Production de composes de carbonyle superieur a partir d'alcools inferieurs Ceased WO1986004057A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB858500107A GB8500107D0 (en) 1985-01-03 1985-01-03 Catalytic reaction
GB8500107 1985-01-03

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Publication Number Publication Date
WO1986004057A1 true WO1986004057A1 (fr) 1986-07-17

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PCT/GB1985/000593 Ceased WO1986004057A1 (fr) 1985-01-03 1985-12-19 Production de composes de carbonyle superieur a partir d'alcools inferieurs

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US (1) US4727196A (fr)
EP (1) EP0188899B1 (fr)
JP (1) JPS62501358A (fr)
CA (1) CA1255331A (fr)
DE (1) DE3562615D1 (fr)
GB (1) GB8500107D0 (fr)
WO (1) WO1986004057A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4876392A (en) * 1982-09-21 1989-10-24 Exxon Research & Engineering Company Process for preparation of keystones by oxidation of secondary alcohols using a trimetallic catalyst comprising molybdenum, rhenium and a group VIII noble metal
DE19630788C1 (de) * 1996-07-31 1997-09-11 Basf Ag Verfahren zur Herstellung von NH¶2¶-Gruppen enthaltenden Verbindungen
DE102011121087A1 (de) * 2011-12-14 2013-06-20 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Verfahren zur katalytischen Kondensation oder Kopplung
CN104588003B (zh) * 2014-12-24 2017-11-07 中国科学院青岛生物能源与过程研究所 一种多相金属催化剂及其在由甲醇和乙醇水溶液制备异丁醇中的应用
CN114956968B (zh) * 2022-01-05 2023-10-27 东华理工大学 一种羰基化合物的制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE960007C (de) * 1951-11-24 1957-03-14 Bataafsche Petroleum Verfahren zur Herstellung hoeherer Ketone durch Umsetzung eines sekundaeren aliphatischen Alkohols mit einem aliphatischen Keton
GB1325911A (en) * 1970-10-05 1973-08-08 Dow Chemical Co Catalysis of the exchange reaction between secondary alcohols and ketones
GB2103649A (en) * 1981-07-28 1983-02-23 Inst Francais Du Petrole Process for methane synthesis by catalytic reduction of carbon monoxide in aqueous phase

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3361828A (en) * 1962-01-02 1968-01-02 Exxon Research Engineering Co Preparation of higher molecular weight ketones
DE1260454B (de) * 1966-07-07 1968-02-08 Rheinpreussen Ag Verfahren zur kontinuierlichen einstufigen Herstellung von gesaettigten Carbonylverbindungen
US3953517A (en) * 1967-09-08 1976-04-27 Veba-Chemie Aktiengesellschaft Process for preparing methyl isobutyl ketone and catalyst
US3781307A (en) * 1969-08-12 1973-12-25 Rhone Poulenc Sa Ruthenium catalyzed process for the alkylation of ketones
US4339606A (en) * 1981-02-06 1982-07-13 Mobil Oil Corporation Conversion of ketones over metal-containing zeolite catalysts
JPS59204145A (ja) * 1983-05-02 1984-11-19 Toa Nenryo Kogyo Kk カルボニル化合物の製造方法
DE3326635A1 (de) * 1983-07-23 1985-01-31 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von monomethylsubstituierten methylen-verbindungen
US4562296A (en) * 1984-11-13 1985-12-31 Ethyl Corporation Production of aldehydes and ketones

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE960007C (de) * 1951-11-24 1957-03-14 Bataafsche Petroleum Verfahren zur Herstellung hoeherer Ketone durch Umsetzung eines sekundaeren aliphatischen Alkohols mit einem aliphatischen Keton
GB1325911A (en) * 1970-10-05 1973-08-08 Dow Chemical Co Catalysis of the exchange reaction between secondary alcohols and ketones
GB2103649A (en) * 1981-07-28 1983-02-23 Inst Francais Du Petrole Process for methane synthesis by catalytic reduction of carbon monoxide in aqueous phase

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Publication number Publication date
CA1255331A (fr) 1989-06-06
DE3562615D1 (en) 1988-06-16
EP0188899A1 (fr) 1986-07-30
JPS62501358A (ja) 1987-06-04
US4727196A (en) 1988-02-23
EP0188899B1 (fr) 1988-05-11
GB8500107D0 (en) 1985-02-13

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